


Give Me a Break

by Loony_Kit



Category: Supernatural
Genre: Multi, Parole!AU, Pre-Relationship, Second Chances, cas is tired of his shit, gabriel getting his way, this is not how you are supposed to law
Language: English
Status: Completed
Published: 2018-02-26
Updated: 2018-02-26
Packaged: 2019-03-24 02:18:28
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,486
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13801293
Author URL: https://archiveofourown.org/users/Loony_Kit/pseuds/Loony_Kit
Summary: *I hope you like dialog*He was band new at this job and he had hoped - been told (no, assured) - that at first, he would be given charges that were on the soft side of the criminal element. Just so he could get the hang of things. This Winchester guy, however, was a late twenty something with a rap sheet that stretched as far back as his early teens. Truancy, public disturbance, disorderly, resisting arrest, countless thefts, trespassing, DUI, and now most recently drug charges. Why Gabriel gave him parole after such a short stint in jail, Castiel couldn’t fathom?





	Give Me a Break

**Author's Note:**

> This is a bit of a WIP. It will be updated in small ways in the coming days. Feel free to point out anything in the comments.

Gabriel has always had a sick sense of humor, and Castiel had constantly said that it would get him into trouble one day. Castiel just wasn’t sure what he was going to tell his father though, after he murdered his brother for giving him this stupid set of case files! 

Honestly!? He was band new at this job and he had hoped - been told (no, assured) - that at first, he would be given charges that were on the soft side of the criminal element. Just so he could get the hang of things. This Winchester guy was a late-twenty-something with a rap sheet that stretched as far back as his early teens. Truancy, public disturbances, disorderly conduct, countless thefts, resisting arrest, trespassing, DUI, and now most recently drug pushing charges. Why Gabriel gave this man parole after such a short stint in jail, Castiel couldn’t fathom...

Regardless, his new charge was scheduled to be here for his first check in over fifteen minutes ago. Castiel had a feeling that this was going to be a very short working relationship. Already slipping in responsibility and a record that goes on for miles, there was no way he was going to make it very long. He'd surely end up right back behind bars within a week. 

Thirty minutes now, Castiel noted with a huff as he drummed his fingers on his desk. He shoved aside the man's open file back into his tilting stack and dug out the files for his afternoon appointments. The officer pushed away from his desk, he really needed another cup of coffee if this was how his day was going to continue. 

As he made his way through the courthouse’s maze of hallways towards the lunch-room, he decided to cut through the lobby, but there was a big commotion baring him from making it across the hall. It seemed that someone was being held up at the entrance by security, and they were none too happy about it. Castiel tried to weave his way through the crowd to get a better look. He could already hear the guy’s voice as it carried over the heads of the gathering.

“This is the stupidest shit ever, I’m obligated to be here and you guys are pulling this bullshit! I don’t know why I even bother!”

“Sir, if you don’t calm down you will be arrested. We aren’t just going to let you wonder around with possibly dangerous items in your pockets. We have to search you.”

“This is some fucking stupid ass bullshit!”

Castiel finally managed to struggle to the front of the throng. The man with the very foul mouth had his leather clad back to Castiel as he continued to exchange words with the head of the courthouse’s security. Many other officers seem to be casually idling around, but Castiel knew they were only feigning nonchalant-ness. They were keeping a wary eye out for any sign that things might get nasty. Which was a good thing to; this guy looked like he was really at the end of his rope. Castiel, wanting details, nudged the woman next to him. As it turned out the man had gone through the metal detector and it kept going off, when he searched his pockets for the fourth time the guards found something that put them on edge, and they had been detaining the man on suspicion ever sense.

Just as the woman finished her explanation, a loud voice rang out over the entire hall. Everyone turned to see his Honor Judge Emmanuel standing at the top of the grand staircase in the middle of the lobby hall. Gabriel Emmanuel - otherwise known as the constant thorn in Castiel’s side - was adorned in the usual court robes and his long gold cords that made it seem as if he was heading off to a graduation; he just couldn’t help but to put his own spin on the normally “boring black drapes”. Even though his stature was lacking he could more than make up for it with his rather grandiose presence. 

Though Castiel knew better, Gabriel’s expression as he surveyed the mob that had gathered was stern and wary. After several tense moments, the mask finally broke. His face split into a wide grin as he leaned an elbow on the banister and his straight posture slumped casually.

“Okay! Look, guys, I know it’s Monday, but you can just hang out in the lobby. You should at least wait until Friday. Besides, it’s not a real party unless I’m invited, am I right? Seriously though…” His grin faded a quick as it had come, his face fell into a half frown half pout, and he propped his fist on his hip. “…why is the entirety of security down here? Someone could be robbing the upper floors blind and we’d all be none the wiser.”

“We have a security threat, Your Honor.” The head officer informed promptly. Gabriel’s eyes darted over towards the guard at his words, and then his eyes slid over to the person standing in front of the officer. The judge's eyes lit up in recognition.

“Of course, it would be you Winchester.” Gabriel drawled as he pushed off the hand rail and started to saunter gracelessly down the stairs towards the two men; the crowd parted like the Red Sea as he approached.

‘Winchester?’ Castiel turned back towards the guy in the leather jacket. This couldn’t possibly be his new charge? ‘Great’ Castiel thought in despair. The profile of the man’s face was now visible as he - like everyone else - was now watching Gabriel. He had a strong jaw which was covered in light stubble and short chestnut hair. His expression was mixed. There was a great deal of defiance and irritation lingering there, but also just the barest hint of respect as he watched Gabriel approach.

“What kind of trouble have you found yourself in today, Dean?” Gabriel asked as he made it up to the security station and leaned on it. Gabriel always had been a leaner.

“We’re searching for weaponry, Sir.”

“Why?!” Gabriel scoffed.

“He went through the metal detector server times and the final time he checked he shook out his coat and a bullet shell was found. We want to search his person, but he is being obstinate.” The officer indicated a bowl that sat on the other side of the security counter.  
‘Oh lord, he has access to weapons.’ Castiel thought with a grimace.

“…for the love of my uncle Pete! That’s the threat!?” Gabriel laughed as he snatched the spent ammunition up out of the container and peered at it closely.

“Where there are bullets there is usually a gun, Your Honor.” The guard said knowingly.

“This is a shell; a damaged one at that; it would jam a gun or blow up in his face if he tried to use it.” Gabriel retorted with a cocked eyebrow.

“We weren’t sure if he had more.” The guard defended.

“Did you send him back through the detector after the bullet casing was found?”

“Yes.”

“… And, did it go off?”

“No…” Gabriel’s face fell at this, but the officer continued “…but we want to be safe.”

“Indeed…” Gabriel said, obviously not listening now. “Dean, go through the detector if you’d please.” The detained man rolled his eye, but did as he was asked. When he made it into the machine he stopped hard and spun on his socked heels to face the judge when has was directly in the middle of the metal detector. The sensor remained silent. He raised his eyebrows exasperatedly and patted his pockets to show he carried nothing except the clothes on his back.

“So you caused a huge traffic jam in my lobby, diverted all of my security from their posts, and…” Gabriel shook out his wrist to check his watch “…made Mr. Winchester late for his mandatory appointment because you found a casing, that he had to shake loose from his jacket. This man’s godfather is Robert Singer and he stays with him on a regular basis. That old coot has a junk yard full of only God knows what. I’m not surprised he has random bullet casing on his person.” Gabriel gripped. He had clearly had enough because he turned to the hall at large. “Alright everyone scram, the shows over! I know for a fact you all have shi… r-um, things to do. Security, I want all of you back to your stations. Now!” Gabriel added for emphasis seeing no one move, there was the immediate sound of people scrambling. As goofy and ridiculous as Gabriel was he was not someone you wanted to cross. Like previously mentioned, he had a sick sense of humor. The lobby started to clear and Castiel tried to shrink back into the mass of moving bodies. Gabriel rounded back on the head of security.

“You…” Gabriel pointed sternly “… back to work” he then looked over at Dean, “get your stuff together and follow me…” Gabriel turned to start back towards the stairs when he hesitated and then almost as an afterthought said, without looking back “…you to Mr. Castiel.” The parole officer flinched, he had hoped that Gabriel hadn’t noticed him. The tall man now identified as Dean Winchester (his newest charge) turned to look over in his direction when Gabriel finally directed a lazily look over his shoulder at him. Castiel wasn’t sure he liked the way Dean cocked his eyebrow when laid eyes on him. Castiel had to take a moment to steady himself before he could followed in his brother’s direction.

“Chop chop, Cassy, we haven’t got all day.” Castiel’s head jerked fully in Gabriel’s direction and he narrowed his eyes. He didn’t like his family’s stupid nicknames. “Don’t give me that sassed out look young man, come on, move it!” Castiel set his jaw and drew himself up to his full height as he took his time mover over towards the judge. Gabriel had always been the smallest male member of the family and though Castiel had always thought himself above the fighting and petty insults his brothers loved to throw around, he couldn’t help but to tower over his brother’s short comings when he intentionally used a nickname to irritate him.

Castiel was careful not to look directly at the man now walking next to him as Gabriel lead the way. He sure didn’t seem to have any qualms about taking his fill though. Castiel could see out of his peripheral that the man's eyes kept darting over in his direction. Castiel’s uneasiness tightened up a few more notches; he was really tempted to snap at him.

‘For the love of God, keep your eyes to yourself!’ Castiel thought, hoping the vibe of the message would translate through his body language. It either didn’t transfer or more likely, the other man just didn’t care that he was making Castiel uncomfortable. After all it’s hard to misinterpret tightly crossed arms and avoiding eye contact.

Once arriving at what Castiel had thought was Gabriel’s chambers, the judge pulled open the door open with a really unnecessary flourish. Dean made no hesitation as he entered the door way, but Castiel as reluctant to follow. Trying to stall, Castle noticed that unbeknownst to him Gabriel had lead them to his own lonely office. How he hadn't noticed that Gabriel didn't lead them up the grand stair case, he wasn't sure.

“We are going to play nicely today, right Cassy?” Gabriel warned playfully as he suddenly pushed Castiel so forcefully over the threshold of his office that he stumbled and nearly fell. When he saw the ground coming up to meet him he clenched his eyes shut and braced himself for the impending pain. Surprisingly, the hard surface he expected never came, instead he met a much softer object that halted his fall.

He looked up to see a very big set of jade eyes and a very bright smile framed by light stubble. Of all the things to look at on the man’s face, his eyes were what caught your attention, but the faint dapple of freckles across the bridge of his nose came in at a close second. Castiel stammered a small thank you as he quickly tried to disentangle himself from the other man’s arms. Castiel looked around and though he was exponentially pissed at Gabriel, he was relieved to see that he had not just pushed him in to the arms of this convict and simply abandoned him. He stood smugly and squarely in the door frame as if he was ready if Castiel tried to run.

“Mr. Winchester this is Castiel Emmanuel, he is your parole officer and my brother, so try not to break him.” Dean glanced a little suspiciously over at Castiel as if this might be some kind of tick, but after a moment a small smile crept across his face again. Then he held out his hand in proper greeting, Castiel purposely took it. He gave a terse nod of acknowledgement “Cassy, this is Dean; keep an eye on him for me. Well, see how you two are all cozy, I’ll leave the two of you aloooone.” Gabriel said with a hinting cock of the eyebrow. Before Castiel could turn to reprimand his brother for the, insinuation, he had already slammed the office door shut.

Castiel gave a weary sigh as he stared at the now closed door.

“So, Cassy, the judge is your brother. How about that…”

“Please…” Castiel said abruptly “…do not call me that.” Dean held up his hand in mock defense. 

"How about simply Cas? You got to admit those biblical names are a bit of a mouthful."

“Feel free to take a seat while I find your paperwork...” Cas sighed, not wanting to drag out this interaction.

Dean sat happily in the more comfortable of the two chars in front of Cas’ desk. Being new meant you got left-overs from the other offices and the mismatched chairs in front of his desk were blatant proof of that. It also meant that you got the smallest office in the building. At best he could only retreat about eight feet away from Dean at any one point in this tiny room.

Castiel, having assumed that Mr. Winchester wasn’t coming to his first appointment he had put all of Dean’s papers away, he tried his best to dig them back out without seeming flustered. Dean watched, chin propped up on the heel of his hand, as Castiel rifled around trying to get everything in order. When Cas finally sat down behind his desk, Dean piped up.

“You're nothing like your brother” he observed, hand still dreamily propping up his head.

“Oh…” Cas responded, spearing Dean a polite glance.

“Well, you seem very straight laced which he’s clearly not.”

“Indeed,” Cas said, not too sure how to take that statement. After filing through all of the folders stacked on his desk he managed to find Dean’s at the bottom of the very last stack. Pulling it out caused the first several to slide off the top of the pile. Castiel quickly tried to halt their fall, but it was no good. They avalanched across his desk. Cas hurriedly tried to re-stack them. Dean leaned forward and attempted to help but after straightening a few files one in particular caught his attention.

“You’re Ruby’s parole officer!?” Dean nearly shouted at the top of his voice. Cas lean forward and snatched the file out of Dean’s hands.

“I will be her parole officer, and these files are private” Castiel grumbled.

“Well you have them all out in the open all over your desk” Dean pointed out. 

Cas gave him a sour look. He was really not in the mood for this. It wasn’t his fault he didn’t have proper storage for all his files. Cas decided to ignore this observation and turn the subject.

“So, you know Ruby Kristy” he hadn’t meant for that to sound as accusatory as it did, but Ruby was… an unsavory character to put it mildly.

“You could say that…” Dean answered vaguely, he seemed to be mirroring Cas’ sour look. Cas wondered what linked the two, he could assume it was drugs seeing how that was a charge they both had in common and they happened around the same time. But something about the darkness that clouded Dean’s eyes when Cas had asked about her gave him the impression they had not left on good terms.

Castiel, having finally reorganized, really just wanted to get on with this meeting. He went over all of the rules and restrictions needed to follow to keep his butt of jail. Dean seemed to visibly relax over the course of the explanations. A smile even seemed to be playing around the corners of his mouth.

When they were finally done and the last paper signed, Cas asked if he had any questions. Dean responded with a genuinely cheerful ‘nope’. As he started to gather up his forms and keys, Castiel allowed himself a large sigh. God, what a day.

“You seem unhappy…” Dean noted before he got up to leave.

“My brother lives to make my life a hellish experience, so I’m not too enthused about any of my case files.”

“Especially mine it seems” Dean said slight dejection.

“I was told I’d be given easier cases when I first started, your file is hardly entry level.”

“On the contrary, I’m quite easy” Dean said with a small, sly smile that Cas didn’t see, but could practically hear dripping from every word in that sentence.

“Indeed…” Castiel frowned, not looking up at Dean from his paperwork.

“Why have you just decided that you don’t like me? You hardly know me.”

“I do not dislike you” Castiel said curtly.

“Dude, you’ve had ‘fuck off’ written all over your body language for like the past hour.”

“Why do you say that?” Castiel asked with only mild interest.

“Because…” Dean said with a slight note of irritation, slapping his hand down on top of the paperwork Cas had shuffled and re-shuffled about three times now "you refuse to look at me for one, plus your tone has been snippy as fuck ever since we first said hello.”

“Your record really speaks for itself Mr. Winchester, and your association with Ms. Ruby does not add to your character references” Castiel retorted, yanking his papers out from under the other man’s hand.

“If you’re going to pre-judge every person that comes in front of you as a parole officer, you're not going to last long in this job. People don’t like it when you look down on them.”

“I’m not looking down on you…” Cas said fully confronting Dean for the first time “… I’m being cautious; beside we aren’t exactly supposed to be friends. I’m fundamentally a professional taddle-tell Mr. Winchester.” Dean’s eye ticked as this, at first Cas thought Dean was rising to leave, but his face was suddenly very close to his own. Cas’ heart rate was running double time with every inch nearer Dean moved. Cas could see every last dumb freckle on his cheek and his eye lashes were ridiculously lovely.

“Just because people do bad things, it doesn’t necessarily make them bad people” Dean said, voice unreasonably clear and oddly calming. Dean straightened back up and pulled his jacket back over his shoulders. Castiel’s fluster must have shown on his face because Dean was sporting a very satisfied smirk. Dean pocketed his keys and crammed his info papers in the other.

“See ya later, Cas” Dean winked with a click of his tongue and with that Dean strolled out of Castiel’s office. Cas was glad he was gone, because he was surely three shades redder. He took a steadying breath and aimlessly shuffled the files on his desk. Cas looked back up towards the now empty doorway.

“Stupid, insufferable … pretty jerk.” Cas huffed as he stood quickly, nearly knocking over his chair, and suddenly snatched up Winchester’s file.

Gabriel did not seem at all surprised when Cas came storming into his chambers and slapped the Winchester file on to his desk.

“Hello dear brother” Gabriel said cheerfully when he looked up from his laptop.

“Don’t you dear brother me! You are such a... Why would you assign me Dean Winchester?” Castiel demanded.

“To be honest, I was hoping that the two of you would be a good influence on each other…” Gabriel said pointedly.

“How on earth could he be a good influence on me!?” Cas asked, exasperated. 

“To be frank my dear Cassy, you have a stick wedged firmly up your ass” Gabriel said matter-of-factly. Cas sputtered at this blunt pronouncement.

“I do not! Even if I did, it’s not for you to decide to send me a career convict to ‘loosen me up.’ ” Castiel said with a sarcastically large set of air quotes.

“Calm down, you’re acting like the world is ending. He’ll teach you to loosen up, you can give him a break he wouldn’t get from the other parole officers, it’s a win-win.”

“What makes you think I’ll go easy on him?” Castiel asked, crossing his arms in mock curiosity.

“Because he’s cute” the judge said as he turned back to his work. Cas’ outrage seemed to have reached its limits. The only reaction he could manage was a very deep sigh while collapsing into one of Gabriel’s very plush guest chairs. 

“Great thanks...” Cas said wearily rubbing his face with his hands “… just what I need, a druggy hinting on me.”

“He’s not a druggy” Gabriel countered dismissively.

“He was jailed for drug possession and he knows Ruby Kristy” the younger brother pointed out. Something a little more serious flicked behind Gabriel’s eyes. He calmly looked up and leaned back in his chair, running his hand through his hair as he considered his brother.

“Why do you think I gave Dean such a short stint in jail?”

“You're mental unstable” Castiel hazarded a guess.

“It’s because for all Dean Winchester’s faults, I know for a fact that those drugs were not his.” 

“That makes no sense. Why would you convict an innocent man?”

“He confessed...”

“Then he did do it” Cas retorted a little irritated now.

“No, he didn’t,” Gabe knowingly corrected.

“Why would he confess to something he didn’t do?” Gabriel's smirk softened ever so slightly at his brother's confusion.

“Because, he was trying to protect his younger brother, Sam. The drugs belonged to him. He apparently met Ruby at a collage, and she wrapped him around her finger tighter than that stick up your ass. He has a full ride to Stanford, any convictions would have resulted in the immediate loss of all of his scholarships and their family ain’t exactly rich.”

“If that’s true, why didn’t you say something?” Cas pondered, his brow becoming increasingly more scrunched together.

“Well I couldn’t prove it for one, and to be fair Dean’s logic is spot on. He’s already got a rap sheet and Sam had a real chance to make something of himself. Dean was giving him a second chance. Last I heard from old Singer, Sam took a semester off school after Dean went to the county lock up to 'clear his head.' Now he’s a year away from graduating. Getting sent to jail would have ruined Sam’s life. Dean’s not as dumb as he seems.”

“If there is no proof then how do you know all this?” Castiel asked in a quite tone.

“Dean is not one to just roll over like that; I’ve seen him fight a red light violation when there was video evidence. Sam and Bobby came to every one of Dean’s hearings, poor dumb kid looked like he was ready to throw up.” Castiel mulled this over for a long moment before the question knocking around in the back of his mind pushed forward.

"What if this, Sam, gets into the same kind of trouble in the future?" Cas retorted. An slightly unsettling, shifty grin came over his bother's face.

"Well, he and Dean are quite close and I think seeing his brother pay for his sins would be enough to knock sense into him, but I'm sure I could think of more creative ways to punish him than jail for break any laws in the future. As a matter of fact, I've made mention of a possible internship position once he's started towards his doctorate."

"Judging from Dean’s age, you must be at least fifteen years older than Sam..."

"Details, my dear Cassy, details" Gabriel waved off.

"You are so unethical."

"...and yet they continue to elect me to the bench, must be something to do with my low recidivism rates; swings and roundabouts" Gabriel shrugged.

“Yeah, well Dean still has a DUI and a million other things on his record.”

“That DUI was bull, he moved his car from a bar parking lot to the one next door to it so he could sleep off his buzz in his car undisturbed and he happened to cross a dirt road that was technically a public street, so he was ‘driving drunk’. That resisting arrest was in the same incident too, the cops waited till he was half asleep before pulling him out of his car. Naturally he fought back not knowing who was in his car. He tried to get back in his car, but they threw him down and arrested him. A bunch of those thefts happened at grocery stores. Like I said their family isn’t rich, in fact you could say they are downright poor. You can’t blame a fifteen-year-old kid with a nine-year-old brother to look after for being hungry. You should really read the police reports that come along with the arrest history outline.” Gabriel said as he dug around in his top draw for his candy stash.

“Oh…” was all Cas could think to say. He wasn’t really too sure what to do with all this new information.

“You should give him at least half a chance Cassy.” Gabriel said with a crafty smile. Cas’ face fell.

“It’s not exactly appropriate for a parole officer to be in a relationship with one of his charges” Castiel grumbled.

“You're only going to be over seeing him for a few months, depending how the judge rules.”

“You are the judge!” Cas snapped back.

“How convenient…” Gabriel drawled as he rolled a sucker around the big evil grin that consumed his face.

Cas could do nothing but narrow his eyes at his scheming brother. He stood from where he was seated and without saying good bye, marched out of Gabriel’s chambers just as irritated as when he arrived. He really needed that coffee he never got if he was going to be reading through police records for the rest of the day.


End file.
